2-(4&#39;-hydroxy-aryl-amino)-aryl-amino-naphthalenes



, eral formula 1 Patented July 21,1931 i RICHARD meats rn NKFoRr N-THn-MAIN, AND WILHELM "HECHTENB'ERG, or -"FRANK}?ORT ON -THE-MAIN FECHENHEIM,r. GERMANY, A$SIGNORS TO GENERAL "*ANILINE woiaxs, 11m; or N wYoRmN. Y; A CORPORATION or {DELAWARE 2-(4'HYDRoXx ARYLAMI qo)has;eii mo mirii'rriiinnnns Our present invention relates to new condensatlon'products corresponding to the gen- V vvhere'in one X means hydrogen, the other X 9 an'arylamino-group and wherein both arylresidues may contain further substituentsQ The new products are obtainable by treating an arylamino hydroxyrnaphthalene carf in b y boxylic acid of thegeneral formula:

r v r j reaction th'ehydro'xygroupiof the naphthalene compound is replaced by a pa'raQhydroxyarylaminorgroup While I the earb oxylic group is simultaneously split ofi;

The arylamino-2+hydroxy-naphthalene=3 carboxylic acids used as starting material in:

this process may "be prepared for instance by condensing a 2.6 or?fig dihydroxy napthalene-3-carboxylic acidwith anaromatic amine in the manner described in U. S. application Serial No. 843,554,' filed February 28, 1929.

t being byw'eight andiall temperatures in centi- ;:-grade degrees. We wish it however to: be

understood; that We are not limited to the particular conditions norto the specific productsmentioned therein. V "E'a;ampZe- 1;

or mixture ofQS partsoft G-phenylaminO-Q- hydroxy-naphthalene-3 carboxylic acid and 16 parts of- 4amino.-phenol is f boiled under a reflux condenser With theadditionof about ,-'-r54;()--parts ofa sodium bisulfite solution of 40,

QB. After about, hoursthemass is cooled 50 and the precipitate is filtered ofi' and Washed tioned phenylamino-compound.

I {In orderto further illustrate our invention the'following examples are given, the parts J .mnra in Applicationtfiled August1 6,"1929, Serial ma er and in Ger an September 1 3, 1928.

with Water, acidified Water and aldilute soda solution. The 2- (tlhydroxyphenylamino) r 6'-phenylamino-naphthalene thus formed ete e WWW h fermu w Accordingif to formula represents a leuco-amphi quinone-imide. It crystallizes from alcohol in the form of brilliant greenish glistening leaflets ofinelting point 205% It is easily soluble in hot alcohol, difiicultly solu- When treated with an alkaline'solution of" hypochlorite or with a'chromate in an acetic uct having probably the constitution of an '7 indopheno'l. a c

When" 6- (4-tolylamino 2- hydroxy naphprocess, 2- (4-hydroxy-phenylainino) -6- (4"- shows similar propertiesas the above men- ,Alsof l-amino-phenol may be replaced by other paraahydroxyarylainines as for instance i E 'aamyiZe 2 i 28 of 8 phenyIaminO 2-hydroxye I naphthalene-3ecarboxylic acid and 16'parts of 4-amino -phenol are treated with sodium bi-:-

sulfite as describedfin Example Q1. "In this in an-n e r 1' a2 '(4Fhydroxyphenylainino) -8- phenylamino-naphthalene of the probable. formula: I c

in a closed vessel under pressure. In 1 this case the duration of reaction is much shorts acid solutionit yields a blue oxidation prod- 7o thalene-3-carboxylic acid is subjected to'this 1y1amino)-napthaie ne is obtained which I t-amin0-2.6-dichloro l-hydroxyfbenzene; a V

We claim: 7 e v -1. As new compounds 2-(4-hydroXy-aryle amino) earylamino naphthalenes of the gen eral formula V I l 10 wherein. one; Ximegnsi hydrog'en-,.fihe= other e an arylamino-group and wherei n botll arylresidues are oft-he benzeneaseries and Ina-y: contain further .snbstituenfis, which, eornpounds are crystallineeubstances; having a 15 definite melting pointibeing; soluble in hot.

alcoholand. capable of being transformed into, blue compounds; by means, oi oxidizing;

' fiigents. T -r 1 f 2. As new compounde 2-(4-hydroxy-ary1-- y amino); 6larylamlilno nglphthalenes of the general formula: I V

wherein both: anyl resi clues areoftlhe benzene series, and" contain further substituenjgs,

Which compounds are crystalline substances;

having mclefiniteIneltingpoint, being soluble l h b; alc h and ealp bi e e' fi f owned intoblue' co mpounds bymeans 01$ z d l i eagemsl r r 1 3. As a new compound, 2-(4 hyd-noxyep eny r min phenyle mo-naph halen 5 mE- tIie fOBm lL which compound cnystalliizes 15mm alcohol in the forml of bnillianc, greenish, glistening leaflets-,- melbing M1205 being so'luloleim hot alcohol, difli'cultly solublei nrbenzene and ber ling Capable of being d d to fo m a blu 40 product, V

tu-res.- v 7 V y Y RICHARDHE'RZL 

